반응 #48617

반응 방정식

sodium chloride

[(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester

ethyl vinyl ether

acetonitrile

N-iodosuccinimide

→

desired compound

수율 34.0%

[(R)-2-(tert-butyl-dimethylsilanyloxy)-1-(1-ethoxy-2-iodoethoxymethyl)-ethyl]-carbamic acid tert-butyl ester

수율 34.0%

반응 조건

후처리

1. 1
   추출Extract with ethyl acetate
2. 2
   세척wash with water and saturated aqueous sodium chloride
3. 3
   건조dry (magnesium sulfate)
4. 4
   여과filter
5. 5
   농축concentrate
6. 6
   기타Purify
7. 7
   세척(silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate)

실험 절차

Dissolve [(R)-1-(tert-butyl-dimethylsilanyloxymethyl)-2-hydroxyethyl]-carbamic acid tert-butyl ester (1.0 g, 3.27 mmol) and ethyl vinyl ether (0.20 g, 2.73 mmol) in acetonitrile (20 mL) and add N-iodosuccinimide (0.735 g, 3.27 mmol). Stir at room temperature 72 hours and pour into saturated aqueous sodium chloride. Extract with ethyl acetate, wash with water and saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate. Purify (silica gel chromatography, eluting with 100:0 to 10:90 hexanes:ethyl acetate) to give the desired compound (462 mg, 34%).

출처